WO2016065680A1 - Dispositif électroluminescent organique vert et son procédé de préparation - Google Patents

Dispositif électroluminescent organique vert et son procédé de préparation Download PDF

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WO2016065680A1
WO2016065680A1 PCT/CN2014/091784 CN2014091784W WO2016065680A1 WO 2016065680 A1 WO2016065680 A1 WO 2016065680A1 CN 2014091784 W CN2014091784 W CN 2014091784W WO 2016065680 A1 WO2016065680 A1 WO 2016065680A1
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layer
electron
light
bis
hole
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周亮
张洪杰
李雅囡
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Changchun Institute of Applied Chemistry of CAS
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Changchun Institute of Applied Chemistry of CAS
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the invention relates to the field of organic electroluminescence technology, in particular to a green organic electroluminescent device and a preparation method thereof.
  • An organic electroluminescent device is a self-luminous device whose principle of illumination is that when an electric charge is injected into an organic layer between a hole injecting electrode and an electron injecting electrode, electrons and holes meet, combine, and then annihilate, thereby generating Light.
  • Organic electroluminescent devices have characteristics such as low voltage, high brightness, and wide viewing angle, and thus organic electroluminescent devices have been rapidly developed in recent years. Among them, green organic electroluminescent devices have become a research hotspot because of their broad application prospects in monochrome display and white light modulation.
  • the trivalent europium complex has been regarded as an ideal organic electroluminescent material by academics and industry because of its high luminous efficiency and adjustable color of light.
  • Many research teams at home and abroad have started from material synthesis and device optimization to improve the comprehensive performance of green organic electroluminescent devices to meet the needs of industrialization.
  • Junji Kido et al. of Yamagata University, Japan used a green-emitting iridium complex Ir(ppy) 3 as a luminescent material, and a green organic electroluminescent device was obtained by doping.
  • the device exhibits an ideal green luminescence, a higher maximum luminescence efficiency is obtained.
  • the unbalanced carrier injection causes the device to decay more efficiently and has a higher operating voltage, which is disadvantageous for improving the brightness and operation of the device. life.
  • the technical problem to be solved by the present invention is to provide a green organic electroluminescent device with high comprehensive performance and a preparation method thereof.
  • a green organic electroluminescent device comprising:
  • the electron-dominated light-emitting layer is composed of an organic sensitizing material, a green organic light-emitting material and an electronic type organic host material;
  • the organic sensitizing material is selected from one or two of tris(acetylacetonate) ruthenium and tris(acetylacetonate) linofoline ruthenium;
  • the organic sensitizing material is from 0.1% by weight to 0.5% by weight of the electronic type organic host material.
  • the content of the green organic light-emitting material is 5 wt% to 10 wt% of the electronic organic host material.
  • the green organic light-emitting material is selected from the group consisting of tris(2-phenylpyridine) ruthenium, bis(2-phenylpyridine)(acetylacetonate) ruthenium, and tris[2-(p-methylphenyl)pyridine. ⁇ , bis(2-phenylpyridine)[2-(diphenyl-3-yl)pyridine] ruthenium, tris(2-(3-p-dimethylphenyl)pyridine ruthenium and tris(2-) One or more of phenyl-3-methyl-pyridine).
  • the electronic organic host material is selected from the group consisting of 2,6-bis[3-(9H-9-carbazolyl)phenyl] Pyridine, 1,4-bis(triphenylsilyl)benzene, 2,2'-bis(4-(9-carbazolyl)phenyl)biphenyl, [2,4,6-trimethyl-3 -(3-pyridyl)phenyl]borane, 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene, 1,3-bis[3,5-di(3-pyridyl) Phenyl]benzene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, 9-(4-t-butylphenyl)-3,6-bis (three) One or more of phenylsilyl)-9H-carbazole and 9-(8-diphenylphosphoryl)-diazo
  • the hole-causing light-emitting layer is composed of a green organic light-emitting material and a hole-type organic host material; the green organic light-emitting material is 5.0 wt% to 10.0 wt% of the hole type organic host material;
  • the green organic light-emitting material is selected from the group consisting of tris(2-phenylpyridine) ruthenium, bis(2-phenylpyridine)(acetylacetonate) ruthenium, and tris[2-(p-methylphenyl)pyridine] ruthenium. , bis(2-phenylpyridine)[2-(diphenyl-3-yl)pyridine] ruthenium, tris(2-(3-p-dimethylphenyl)pyridine ruthenium and tris(2-phenyl-) One or more of 3-methyl-pyridine);
  • the hole-type organic host material is selected from the group consisting of 4,4'-N, N'-dicarbazole diphenyl, 1,3-dioxazole-9-ylbenzene, 9,9'-(5-(three Phenylsilyl)-1,3-phenyl)di-9H-carbazole, 1,3,5-tris(9-oxazolyl)benzene, 4,4',4"-tris(carbazole-9 One or more of triphenylamine and 1,4-bis(triphenylsilyl)biphenyl.
  • the material of the hole transporting-electron blocking layer is selected from the group consisting of 4,4'-cyclohexyl bis[N,N-bis(4-methylphenyl)aniline], dipyrazine [2,3-f :2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile, N4,N4'-di(naphthalen-1-yl)-N4,N4'-double ( 4-vinylphenyl)biphenyl-4,4'-diamine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-2,7-diamine -9,9-spirobiguanide, N,N,N',N'-tetrakis(3-methylphenyl)-3-3'-dimethyl-p-diaminobiphenyl, 2,2'-di (3-(N,N-di-p-tolylamino)pheny
  • the material of the hole blocking-electron transport layer is selected from the group consisting of tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane, 1,3,5-tri [ (3-pyridine)-3-phenyl]benzene, 1,3-bis[3,5-bis(3-pyridyl)phenyl]benzene and 1,3,5-tris(1-phenyl-1H- One or more of benzimidazol-2-yl)benzene.
  • the anode modification layer has a thickness of 1 to 10 nm
  • the hole transport-electron barrier layer has a thickness of 30 to 60 nm
  • the hole-dominant light-emitting layer has a thickness of 5 to 20 nm.
  • the thickness of the layer is 5 to 20 nm
  • the thickness of the hole blocking-electron transport layer is 30 to 60 nm
  • the thickness of the cathode modification layer is 0.8 to 1.2 nm
  • the thickness of the cathode layer is 90 to 300 nm.
  • the present application also provides a method for preparing a green organic electroluminescent device, comprising:
  • the anode layer on the substrate is etched, and after drying, the anode modification layer, the hole transport-electron barrier layer, the hole-dominant light-emitting layer, the electron-dominated light-emitting layer, and the hole blocking are sequentially deposited on the anode layer.
  • the electron-dominated light-emitting layer is composed of an organic sensitizing material, a green organic light-emitting material and an electronic type organic host material;
  • the organic sensitizing material is selected from one or two of tris(acetylacetonate) ruthenium and tris(acetylacetonate) linofoline ruthenium;
  • the organic sensitizing material is from 0.1% by weight to 0.5% by weight of the electronic type organic host material.
  • the evaporation rate of the anode modification layer is 0.01-0.05 nm/s
  • the host material in the hole transport-electron blocking layer, the hole-dominant light-emitting layer, the electron-dominated light-emitting layer and the hole blocking-electron transport layer The evaporation rate is 0.05-0.1 nm/s
  • the evaporation rate of the organic sensitizing material in the electron-dominated light-emitting layer is 0.00005-0.0005 nm/s
  • the green light-emitting layer and the hole-priming light-emitting layer emit green light.
  • the evaporation rate of the material is 0.0025 to 0.01 nm/s
  • the evaporation rate of the cathode modification layer is 0.005 to 0.05 nm/s
  • the evaporation rate of the cathode layer is 0.5 to 2.0 nm/s.
  • the present application provides a green organic electroluminescent device comprising a substrate, an anode layer, an anode modification layer, a hole transport-electron barrier layer, a hole-dominant light-emitting layer, an electron-dominated light-emitting layer, A hole blocking-electron transport layer, a cathode modification layer, and a cathode layer.
  • the luminescent material of the present application is a green luminescent material. When electrons and holes are respectively injected into the luminescent layer, electrons and holes will meet and recombine, thereby generating an exciton, and the excitons will transfer energy to the green in the luminescent layer.
  • the molecules of the luminescent material excite an electron to an excited state, and the excited state electrons return to the ground state by a radiation transition to generate a green photon, thereby causing the organic electroluminescent device to emit green light.
  • one or two of tris(acetylacetonate) ruthenium and tris(acetylacetonate) linofol oxalate are added as an organic sensitizing material in an electron-dominated light-emitting layer to make their energy levels and triplet energy.
  • the organic sensitizing material functions as a carrier deep-binding center and an energy transfer step in the electroluminescence process, and can not only improve the material from the host material to the luminescence.
  • the energy transfer of the material can also balance the distribution of electrons and holes in the light-emitting interval, thereby improving the luminous efficiency of the organic electroluminescent device, improving the spectral stability of the device, reducing the operating voltage of the device, delaying the efficiency degradation of the device, and improving the device. Working life.
  • FIG. 1 is a schematic structural view of a green organic electroluminescent device of the present invention.
  • Example 2 is a graph showing voltage-current density-luminance characteristics of a green organic electroluminescent device prepared in Example 1 of the present invention
  • Example 3 is a graph showing current density-power efficiency-current efficiency characteristics of a green organic electroluminescent device prepared in Example 1 of the present invention
  • Example 4 is a spectrum diagram of a green organic electroluminescent device prepared in Example 1 of the present invention at a luminance of 20,000 cd/m 2 .
  • the embodiment of the invention discloses a green organic electroluminescent device, comprising:
  • the electron-dominated light-emitting layer is composed of an organic sensitizing material, a green organic light-emitting material and an electronic type organic host material;
  • the organic sensitizing material is selected from one or two of tris(acetylacetonate) ruthenium and tris(acetylacetonate) linofoline ruthenium;
  • the organic sensitizing material is from 0.1% by weight to 0.5% by weight of the electronic type organic host material.
  • OLED organic electroluminescent device
  • the organic electroluminescent device is made to emit green light.
  • the green organic electroluminescent device of the present application comprises a substrate, an anode layer, an anode modification layer, a hole transport-electron blocking layer, a hole-dominant light-emitting layer, an electron-dominated light-emitting layer, a hole blocking-electron transport layer, and a cathode modification.
  • the layer and the cathode layer are sequentially connected to each other.
  • the hole-bearing light-emitting layer and the electron-dominated light-emitting layer are light-emitting layers of a green organic electron-emitting device.
  • the electronic dominant light-emitting layer of the invention is composed of an organic sensitizing material, a green organic light-emitting material and an electronic organic organic material, wherein the organic sensitizing material plays a sensitizing role in the electroluminescence process to improve the light from the host material to the light-emitting material.
  • the energy of the material transfers and balances the distribution of electrons and holes in the light-emitting interval; the molecules of the green organic light-emitting material are dispersed in the electron-dominated light-emitting layer as a light-emitting center; the electronic-type organic host material acts as a matrix to provide electron transport capability.
  • the energy level and the triplet energy of the organic sensitizing material need to match the energy level of the host material, the luminescent material, and the triplet energy to balance the distribution of electrons and holes in the light-emitting interval and accelerate
  • the energy transfer from the host material to the luminescent material enables the green organic electroluminescent device to have better overall performance. Therefore, the present application selects a rare earth complex selected from a tris(acetylacetonate) ruthenium (Tb(acac) having a structure of the formula (IX) by selecting an illuminating material. 3 ) and one or both of tris(acetylacetonate) linofene ruthenium (Tb(acac) 3 phen) having the structure of formula (X);
  • the doping concentration of the organic sensitizing material in the electron-based light-emitting layer of the present invention affects the performance of the organic electroluminescent device. If the doping concentration of the organic sensitizing material is too low, the sensitizing effect is unsatisfactory, and if the doping concentration is too high, the overall performance of the organic electroluminescent device is lowered. Therefore, the organic sensitizing material is from 0.1% by weight to 0.5% by weight, preferably from 0.2% by weight to 0.3% by weight, of the electronic type organic host material.
  • the green organic light-emitting material in the electron-based light-emitting layer is a light-emitting material well known to those skilled in the art, and the present application is not particularly limited, but in order to make the light-emitting effect better, the green organic light-emitting material is preferentially selected.
  • the doping concentration of the green organic light-emitting material also affects the overall performance of the green organic electroluminescent device. If the doping concentration of the green organic light-emitting material is too low, the device efficiency is low and the color purity is not ideal. If the doping concentration is too high, the luminescent material molecules are agglomerated to form quenching molecules, and finally the device is integrated. performance. Therefore, the electricity
  • the green organic light-emitting material in the sub-primary light-emitting layer is preferably 5 wt% to 10 wt%, more preferably 7 wt% to 9 wt% of the electron type organic host material.
  • the electronic type host material functions as a matrix in the electron-dominated light-emitting layer to provide electron transport capability, and the electronic type host material is a material well known to those skilled in the art, and as a preferred embodiment, the electronic type host material is preferentially selected.
  • the hole-preferred light-emitting layer described in the present application is composed of a green organic light-emitting material and a hole-type organic host material, wherein molecules of the green organic light-emitting material are dispersed in the hole-dominant light-emitting layer as a light-emitting center.
  • the green organic light-emitting material is preferably 5.0 wt% to 10.0 wt%, more preferably 7.0 wt% to 9.0 wt% of the hole type organic host material in the hole-cavity light-emitting layer; the green organic light-emitting If the doping concentration of the material is too low, the device efficiency is low and the color purity is not ideal.
  • the hole-type host material functions as a matrix to provide hole transporting ability.
  • the green organic light-emitting material in the hole-priming light-emitting layer described in the present application is preferably selected from tris(2-phenylpyridine) ruthenium (Ir(ppy) 3 ) having a structure of the formula (II 1 ), having the formula (II) 2 ) a structure of bis(2-phenylpyridine)(acetylacetonate) ruthenium (Ir(ppy) 2 (acac)), a tris[2-(p-methylphenyl)pyridine having the structure of formula (II 3 ) ⁇ (Ir(mppy) 3 ), bis(2-phenylpyridine)[2-(diphenyl-3-yl)pyridine] ruthenium (Ir(ppy) 2 (with structure of formula (II 4
  • the hole-type organic host material is preferably selected from the group consisting of 4,4'-N,N'-dicarbazole diphenyl (CBP) having the structure of formula (III), and 1,3-two having the structure of formula (IV) Carbazole-9-ylbenzene (mCP), 9,9'-(5-(triphenylsilyl)-1,3-phenyl)di-9H-carbazole (SimCP) having the structure of formula (V) 1,3,5-tris(9-carbazolyl)benzene (TCP) having the structure of formula (VI), 4,4',4"-tris(carbazole-9-yl) having the structure of formula (VII) And one or more of triphenylamine (TcTa) and 1,4-bis(triphenylsilyl)biphenyl (BSB) having the structure of formula (VIII);
  • CBP 4,4'-N,N'-dicarbazole diphenyl
  • mCP Carbazo
  • the substrate may be a glass substrate, a quartz substrate, a polycrystalline silicon substrate, a single crystal silicon substrate or a graphene film substrate, and there is no particular limitation in the present application.
  • the anode layer is preferably selected from indium tin oxide (ITO), and its surface resistance is preferably 5 to 25 ⁇ .
  • ITO indium tin oxide
  • the anode modification layer can lower the driving voltage and accelerate the injection of holes, and the anode modification layer is preferably molybdenum oxide (MoO 3 ).
  • the hole transport-electron blocking layer described in this application functions to transport holes and block electrons.
  • the material of the hole transport-electron blocking layer is preferably selected from 4,4'-cyclohexyl bis[N,N-bis(4-methylphenyl)aniline] (TAPC) having the structure of the formula (I 1 ), Dipyrazine [2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) having the structure of formula (I 2 ) N4,N4'-bis(naphthalen-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine (VNPB) having the structure of formula (I 3 ) N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-2,7-diamine-9,9-spirobifluorene having the structure of formula (I 4
  • the hole blocking-electron transporting layer functions to block holes and transport electrons to promote electron injection.
  • the material of the hole blocking-electron transport layer is preferably selected from tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane (3TPYMB) having the structure of the formula (XIV), 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene (TmPyMB) having the structure (XV), 1,3-bis[3,5-di ((3,5-di) having the structure of formula (XVI) 3-pyridyl)phenyl]benzene (BmPyPhB) and one of 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi) having the structure of formula (XVII) Species or more;
  • the function of the cathode modification layer described in the present application is to lower the driving voltage and accelerate the injection of electrons, and the cathode modification layer is preferably lithium fluoride.
  • the cathode layer is preferably aluminum.
  • the material of the hole transport-electron blocking layer, the green organic luminescent material, and the space The source of the material of the organic organic material, the organic sensitizing material, the electronic organic organic material, and the hole blocking-electron transporting layer is not particularly limited and can be obtained by a method well known to those skilled in the art.
  • the anode layer and the cathode layer intersect each other to form a light-emitting region of the device.
  • the thickness of each layer in the green organic electroluminescent device of the present application has a great influence on the device, if the thickness is low. This will result in faster device efficiency degradation. If the thickness is higher, the device will operate at a higher voltage and have a lower lifetime.
  • the thickness of the anode modification layer is preferably from 1 to 10 nm
  • the thickness of the hole transport-electron barrier layer is preferably from 30 to 60 nm
  • the thickness of the hole-preferred light-emitting layer is preferably from 5 to 20 nm
  • the thickness of the electron-dominated light-emitting layer is preferably 5 to 20 nm
  • the thickness of the hole blocking-electron transport layer is preferably 30 to 60 nm
  • the thickness of the cathode modified layer is preferably 0.8 to 1.2 nm
  • the thickness of the cathode layer is preferably 90 to 300 nm.
  • the application also provides a preparation method of the green organic electroluminescent device, comprising:
  • the anode layer on the substrate is etched, and after drying, the anode modification layer, the hole transport-electron barrier layer, the hole-dominant light-emitting layer, the electron-dominated light-emitting layer, and the hole blocking are sequentially deposited on the anode layer.
  • the hole-dominant light-emitting layer is formed by mixing a green organic light-emitting material and a hole-type organic host material;
  • the electron-dominated light-emitting layer is composed of an organic sensitizing material, a green organic light-emitting material and an electronic type organic host material;
  • the organic sensitizing material is selected from one or both of tris(acetylacetonate) ruthenium having a structure of the formula (IX) and tris(acetylacetonate) linofol oxalate having a structure of the formula (X);
  • the organic sensitizing material is 0.1 wt% to 0.5 wt% of the electronic type organic host material
  • the preparation method of the green organic electroluminescent device is specifically as follows:
  • the anode layer on the substrate is laser etched into strip electrodes, and then ultrasonically washed with washing liquid and deionized water for 10-20 min and placed in an oven for drying;
  • the dried substrate is placed in a pretreatment vacuum chamber, and subjected to a low pressure plasma treatment for 1 to 10 minutes under a vacuum of 8 to 15 Pa in an atmosphere of 350 to 500 V, and then transferred to an organic vapor deposition chamber;
  • the anode modification layer, the hole transport-electron barrier layer, the hole-dominant light-emitting layer, the electron-dominated light-emitting layer, and the hole blocking-electron transport are sequentially deposited on the anode layer.
  • the unfinished device was transferred to a metal deposition chamber, and the cathode modified layer and the metal cathode layer were sequentially evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa.
  • the present application achieves deposition of a material by controlling the evaporation rate.
  • the evaporation rate of the anode modification layer is controlled to be 0.01 to 0.05 nm/s, and the host material in the hole transport-electron blocking layer, the hole-dominant light-emitting layer, the electron-dominated light-emitting layer, and the hole blocking-electron transport layer
  • the evaporation rate is controlled at 0.05-0.1 nm/s
  • the evaporation rate of the organic sensitizing material is controlled at 0.00005-0.0005 nm/s
  • the evaporation rate of the green organic luminescent material is controlled at 0.0025-0.01 nm/s
  • the evaporation rate of the cathode modified layer is controlled.
  • the evaporation rate of the metal cathode layer is controlled to be 0.5 to 2.0 nm/s.
  • the vapor-emitting holes dominate the light-emitting layer, wherein the green organic light-emitting material and the hole-type organic host material are simultaneously evaporated in different evaporation sources, and the doped green organic light-emitting materials and holes are controlled by controlling the evaporation rates of the two materials.
  • the weight ratio of the organic organic material is controlled between 5.0% and 10.0%; when the electron-emitting electron dominates the light-emitting layer, the organic sensitizing material, the green organic light-emitting material, and the electronic organic organic material are simultaneously evaporated in different evaporation sources.
  • the mass ratio of the doped organic sensitizing material and the electronic type organic host material is controlled to be between 0.1% and 0.5%, so that the doped green organic luminescent material and the electronic organic organic material are The mass ratio is controlled at 5.0% to 10.0% between.
  • the present application provides a green organic electroluminescent device in which a rare earth complex having a matched energy level distribution, such as Tb(acac) 3 or Tb (acac), is selected among electron-dominated light-emitting layers in the green organic electroluminescent device.
  • a rare earth complex having a matched energy level distribution such as Tb(acac) 3 or Tb (acac)
  • 3 phen as an organic sensitizing material, which plays the role of electron deep-binding center, which is beneficial to balance the distribution of carriers and broaden the light-emitting interval of the device, thereby improving the luminous efficiency of the device, reducing the operating voltage of the device, and delaying the device.
  • the organic sensitizing material has matched triplet energy, functions as an energy transfer step, accelerates energy transfer from the host material to the luminescent material, and relieves luminescent material carriers
  • the problem of luminescence of the host material caused by insufficient capture capability, thereby improving the spectral stability of the device and reducing the dependence of device performance on the doping concentration of the luminescent material.
  • FIG. 1 is a schematic structural view of a green organic electroluminescent device according to the present invention, wherein 1 is a glass substrate, 2 is an anode layer, 3 is an anode modification layer, and 4 is a hole transport-electron blocking layer, 5 The hole is the luminescent layer, 6 is the electron-dominated luminescent layer, 7 is the hole blocking-electron transport layer, 8 is the cathode modified layer, and 9 is the metal cathode layer.
  • the ITO anode layer on the ITO glass was first laser etched into strip electrodes, which were then ultrasonically cleaned with cleaning solution and deionized water for 15 min and placed in an oven for drying. Next, the dried substrate was placed in a pretreatment vacuum chamber, and the ITO anode was subjected to low pressure plasma treatment for 3 minutes under a vacuum of 10 Pa in an atmosphere of 400 V, and then transferred to an organic vapor deposition chamber. In an organic vapor deposition chamber having a degree of vacuum of 1 to 2 ⁇ 10 -5 Pa, a 3 nm-thick MoO 3 anode modification layer 3 and a 40 nm-thick TAPC hole-transport-electron barrier layer 4, 10 nm are sequentially deposited on the ITO layer.
  • Thick Ir(ppy) 3 doped TcTa hole-dominated luminescent layer 5 10 nm thick Tb(acac) 3 phen and Ir(ppy) 3 co-doped CzSi electron-dominated luminescent layer 6 and 40 nm thick TmPyPB hole blocking- Electron transport layer 7.
  • the unfinished device was transferred to a metal deposition chamber, and a 1.0 nm thick LiF cathode modification layer 8 was evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa, and finally passed through a special mask on the LiF layer.
  • a 120 nm thick metal Al cathode layer 9 was deposited to prepare a structure of ITO/MoO 3 /TAPC/Ir(ppy) 3 (7%): TcTa/Tb(acac) 3 phen(0.2%): Ir(ppy) 3 (7%): Organic electroluminescent device of CzSi/TmPyPB/LiF/Al.
  • the evaporation rate of MoO 3 in the anode modification layer 3 is controlled at 0.01 nm/s, and the evaporation rate of TAPC in the hole transport-electron blocking layer 4 is controlled at 0.05 nm/s, and the hole dominates the Ir(ppy) 3 in the light-emitting layer 5 and
  • the evaporation rate of TcTa is controlled at 0.0035 nm/s and 0.05 nm/s, respectively.
  • the evaporation rates of Tb(acac) 3 phen, Ir(ppy) 3 and CzSi in the electron-dominated luminescent layer 6 are controlled at 0.0001 nm/s and 0.0035 nm, respectively.
  • the evaporation rate of TmPyPB in the hole blocking-electron transport layer 7 is controlled at 0.05 nm/s
  • the evaporation rate of LiF in the cathode modified layer 8 is controlled at 0.005 nm/s
  • Al in the metal cathode layer 9 The evaporation rate was controlled at 1.0 nm/s.
  • FIG. 2 is a voltage-current density-luminance characteristic curve of the green organic electroluminescent device prepared in the present embodiment, wherein the curve ⁇ in FIG. 2 is the current density-voltage curve of the device, and the ⁇ curve is the brightness of the device.
  • - Voltage curve according to Figure 2, the brightness of the device increases with the increase of current density and driving voltage, the device's starting voltage is 2.8 volts, the voltage is 9.6 volts, and the current density is 512.37 mA per square centimeter. At (mA/cm 2 ), the device achieved a maximum brightness of 128,905 candelas per square meter (cd/m 2 ).
  • FIG. 3 is a current density-power efficiency-current efficiency characteristic curve of the green organic electroluminescent device prepared in the embodiment.
  • the maximum current efficiency of the device is 126.60 cd/A, and the maximum power is obtained.
  • the efficiency is 141.97 lm / W.
  • FIG. 4 is a spectrum diagram of the green organic electroluminescent device provided by the present invention at a luminance of 20000 cd/m 2 .
  • the main peak of the spectrum is located at 515 nm.
  • the color coordinates of the device are (0.254, 0.651).
  • the ITO anode layer on the ITO glass was first laser etched into strip electrodes, which were then ultrasonically cleaned with cleaning solution and deionized water for 15 min and placed in an oven for drying. Next, the dried substrate was placed in a pretreatment vacuum chamber, and the ITO anode was subjected to low pressure plasma treatment for 3 minutes under a vacuum of 10 Pa in an atmosphere of 400 V, and then transferred to an organic vapor deposition chamber. In an organic vapor deposition chamber having a degree of vacuum of 1 to 2 ⁇ 10 -5 Pa, a 3 nm-thick MoO 3 anode modification layer 3 and a 40 nm-thick TAPC hole-transport-electron barrier layer 4, 10 nm are sequentially deposited on the ITO layer.
  • the unfinished device was transferred to a metal deposition chamber, and a 1.0 nm thick LiF cathode modification layer 8 was evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa, and finally passed through a special mask on the LiF layer.
  • a 120 nm thick metal Al cathode layer 9 was deposited to prepare a structure of ITO/MoO 3 /TAPC/Ir(ppy) 3 (7%): mCP/Tb(acac) 3 phen(0.2%): Ir(ppy) 3 (7%): Organic electroluminescent device of 26DCzPPy/TmPyPB/LiF/Al.
  • the evaporation rate of MoO 3 in the anode modification layer 3 is controlled at 0.01 nm/s, and the evaporation rate of TAPC in the hole transport-electron blocking layer 4 is controlled at 0.05 nm/s, and the hole dominates the Ir(ppy) 3 in the light-emitting layer 5 and
  • the evaporation rates of mCP are controlled at 0.0035 nm/s and 0.05 nm/s, respectively.
  • the evaporation rates of Tb(acac) 3 phen, Ir(ppy) 3 and 26DCzPPy in electron-dominated luminescent layer 6 are controlled at 0.0001 nm/s and 0.0035 nm, respectively.
  • the evaporation rate of TmPyPB in the hole blocking-electron transport layer 7 is controlled at 0.05 nm/s
  • the evaporation rate of LiF in the cathode modified layer 8 is controlled at 0.005 nm/s
  • Al in the metal cathode layer 9 The evaporation rate was controlled at 1.0 nm/s.
  • the performance of the green organic electroluminescent device prepared in this example was examined.
  • the experimental results show that the device emits green light at about 515 nm under the driving of a DC power source.
  • the brightness is 20000 cd/m 2
  • the color coordinates of the device are (0.252, 0.654); as the operating voltage changes, the color coordinates of the device are almost unchanged.
  • the device has a starting voltage of 2.9 volts and a maximum brightness of 126589 cd/m 2 .
  • the device has a maximum current efficiency of 125.22 cd/A and a maximum power efficiency of 135.58 lm/W.
  • the ITO anode layer on the ITO glass was first laser etched into strip electrodes, which were then ultrasonically cleaned with cleaning solution and deionized water for 15 min and placed in an oven for drying. Next, the dried substrate was placed in a pretreatment vacuum chamber, and the ITO anode was subjected to low pressure plasma treatment for 3 minutes under a vacuum of 10 Pa in an atmosphere of 400 V, and then transferred to an organic vapor deposition chamber. In an organic vapor deposition chamber having a degree of vacuum of 1 to 2 ⁇ 10 -5 Pa, a 3 nm-thick MoO 3 anode modification layer 3 and a 40 nm-thick TAPC hole-transport-electron barrier layer 4, 10 nm are sequentially deposited on the ITO layer.
  • Thick Ir(ppy) 3 doped TcTa hole-dominated luminescent layer 5 10 nm thick Tb(acac) 3 and Ir(ppy) 3 co-doped 26DCzPPy electron-dominated luminescent layer 6 and 40 nm thick TmPyPB hole-blocking-electron Transport layer 7.
  • the unfinished device was transferred to a metal deposition chamber, and a 1.0 nm thick LiF cathode modification layer 8 was evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa, and finally passed through a special mask on the LiF layer.
  • a 120 nm thick metal Al cathode layer 9 was deposited to prepare a structure of ITO/MoO 3 /TAPC/Ir(ppy) 3 (7%): TcTa/Tb(acac) 3 (0.3%): Ir(ppy) 3 ( 7%): Organic electroluminescent device of 26DCzPPy/TmPyPB/LiF/Al.
  • the evaporation rate of MoO 3 in the anode modification layer 3 is controlled at 0.01 nm/s, and the evaporation rate of TAPC in the hole transport-electron blocking layer 4 is controlled at 0.05 nm/s, and the hole dominates the Ir(ppy) 3 in the light-emitting layer 5 and
  • the evaporation rate of TcTa is controlled at 0.0035 nm/s and 0.05 nm/s, respectively.
  • the evaporation rates of Tb(acac) 3 , Ir(ppy) 3 and 26DCzPPy in the electron-dominated luminescent layer 6 are controlled at 0.0003 nm/s and 0.007 nm/ respectively.
  • the evaporation rate of TmPyPB in the hole blocking-electron transport layer 7 is controlled at 0.05 nm/s
  • the evaporation rate of LiF in the cathode modified layer 8 is controlled at 0.005 nm/s
  • the Al of the metal cathode layer 9 is The evaporation rate was controlled at 1.0 nm/s.
  • the performance of the green organic electroluminescent device prepared in the present example was examined.
  • the experimental results show that the device emits green light at about 515 nm under the driving of a DC power source.
  • the brightness is 20000 cd/m 2
  • the color coordinates of the device are (0.258, 0.647); as the operating voltage changes, the color coordinates of the device are almost unchanged.
  • the device has a starting voltage of 2.9 volts and a maximum brightness of 118966 cd/m 2 .
  • the device has a maximum current efficiency of 125.68 cd/A and a maximum power efficiency of 136.08 lm/W.
  • the ITO anode layer on the ITO glass was first laser etched into strip electrodes, which were then ultrasonically cleaned with cleaning solution and deionized water for 15 min and placed in an oven for drying. Next, the dried substrate was placed in a pretreatment vacuum chamber, and the ITO anode was subjected to low pressure plasma treatment for 3 minutes under a vacuum of 10 Pa in an atmosphere of 400 V, and then transferred to an organic vapor deposition chamber.
  • a 5 nm-thick MoO 3 anode-modified layer 3 and a 30 nm-thick TAPC hole-transport-electron-blocking layer 4 15 nm were sequentially deposited on the ITO layer.
  • the unfinished device was transferred to a metal deposition chamber, and a 1.1 nm thick LiF cathode modification layer 8 was evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa, and finally passed through a special mask on the LiF layer.
  • a 250 nm thick metal Al cathode layer 9 was deposited to prepare a structure of ITO/MoO 3 /TAPC/Ir(ppy) 3 (acac) (7%): mCP/Tb(acac) 3 (0.1%): Ir (ppy 3 (acac) (7%): an organic electroluminescent device of 26DCzPPy/3TPYMB/LiF/Al.
  • the evaporation rate of MoO 3 in the anode modification layer 3 is controlled at 0.02 nm/s
  • the evaporation rate of TAPC in the hole transport-electron barrier layer 4 is controlled at 0.06 nm/s
  • the hole dominates the Ir(ppy) 3 in the light-emitting layer 5
  • the evaporation rates of acac) and mCP are controlled at 0.007 nm/s and 0.1 nm/s, respectively.
  • the evaporation rates of Tb(acac) 3 , Ir(ppy) 3 (acac) and 26DCzPPy in electron-dominated luminescent layer 6 are controlled at 0.0001 nm, respectively.
  • the evaporation rate of 3TPYMB in the hole blocking-electron transport layer 7 is controlled at 0.08 nm/s
  • the evaporation rate of LiF in the cathode modified layer 8 is controlled at 0.008 nm/s
  • metal The evaporation rate of Al in the cathode layer 9 was controlled at 0.9 nm/s.
  • the performance of the green organic electroluminescent device prepared in the present example was examined.
  • the experimental results show that the device emits green light at about 515 nm under the driving of a DC power source.
  • the brightness is 20000 cd/m 2
  • the color coordinates of the device are (0.255, 0.649); as the operating voltage changes, the color coordinates of the device are almost unchanged.
  • the device has a starting voltage of 2.9 volts and a maximum brightness of 109116 cd/m 2 .
  • the device has a maximum current efficiency of 121.17 cd/A and a maximum power efficiency of 131.20 lm/W.
  • the ITO anode layer on the ITO glass was first laser etched into strip electrodes, which were then ultrasonically cleaned with cleaning solution and deionized water for 15 min and placed in an oven for drying. Next, the dried substrate was placed in a pretreatment vacuum chamber, and the ITO anode was subjected to low pressure plasma treatment for 3 minutes under a vacuum of 10 Pa in an atmosphere of 400 V, and then transferred to an organic vapor deposition chamber. In an organic vapor deposition chamber having a degree of vacuum of 1 to 2 ⁇ 10 -5 Pa, a 6 nm-thick MoO 3 anode modification layer 3 and a 50 nm-thick TAPC hole-transport-electron barrier layer 4, 12 nm are sequentially deposited on the ITO layer.
  • Thick Ir(mppy) 3 doped TCP hole-dominated luminescent layer 5 16 nm thick Tb(acac) 3 phen and Ir(mppy) 3 co-doped UGH2 electron-dominated luminescent layer 6 and 45 nm thick BmPyPhB hole blocking- Electron transport layer 7.
  • the unfinished device was transferred to a metal deposition chamber, and a 1.1 nm thick LiF cathode modification layer 8 was evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa, and finally passed through a special mask on the LiF layer.
  • a 240 nm thick metal Al cathode layer 9 was deposited to prepare a structure of ITO/MoO 3 /TAPC/Ir(mppy) 3 (6%): TCP/Tb(acac) 3 phen (0.3%): Ir(mppy) 3 (6%): Organic electroluminescent device of UGH2/BmPyPhB/LiF/Al.
  • the evaporation rate of MoO 3 in the anode modification layer 3 is controlled at 0.01 nm/s, and the evaporation rate of TAPC in the hole transport-electron blocking layer 4 is controlled at 0.08 nm/s, and the hole dominates the Ir(mppy) 3 in the light-emitting layer 5 and
  • the evaporation rate of TCP is controlled at 0.006 nm/s and 0.1 nm/s, respectively.
  • the evaporation rates of Tb(acac) 3 phen, Ir(mppy) 3 and UGH2 in the electron-dominated luminescent layer 6 are controlled at 0.0003 nm/s and 0.006 nm, respectively.
  • the evaporation rate of BmPyPhB in the hole blocking-electron transport layer 7 is controlled at 0.09 nm/s
  • the evaporation rate of LiF in the cathode modified layer 8 is controlled at 0.012 nm/s
  • Al in the metal cathode layer 9 The evaporation rate was controlled at 1.2 nm/s.
  • the performance of the green organic electroluminescent device prepared in the present example was examined.
  • the experimental results show that the device emits green light at about 515 nm under the driving of a DC power source.
  • the brightness is 20000 cd/m 2
  • the color coordinates of the device are (0.255, 0.652); as the operating voltage changes, the color coordinates of the device are almost unchanged.
  • the device has a starting voltage of 2.9 volts and a maximum brightness of 114598 cd/m 2 .
  • the device has a maximum current efficiency of 124.35 cd/A and a maximum power efficiency of 134.64 lm/W.
  • the ITO anode layer on the ITO glass was first laser etched into strip electrodes, which were then ultrasonically cleaned with cleaning solution and deionized water for 15 min and placed in an oven for drying. Next, the dried substrate was placed in a pretreatment vacuum chamber, and the ITO anode was subjected to low pressure plasma treatment for 3 minutes under a vacuum of 10 Pa in an atmosphere of 400 V, and then transferred to an organic vapor deposition chamber. In an organic vapor deposition chamber having a degree of vacuum of 1 to 2 ⁇ 10 -5 Pa, a 3 nm-thick MoO 3 anode modification layer 3 and a 40 nm-thick TAPC hole-transport-electron barrier layer 4, 10 nm are sequentially deposited on the ITO layer.
  • Thick Ir(ppy) 2 (m-bppy) doped BSB hole-dominated luminescent layer 5 10 nm thick Tb(acac) 3 phen and Ir(ppy) 2 (m-bppy) co-doped BCBP electron-dominated luminescent layer 6 and 40 nm thick TPBi hole blocking-electron transport layer 7.
  • the unfinished device was transferred to a metal deposition chamber, and a 1.0 nm thick LiF cathode modification layer 8 was evaporated in a vacuum atmosphere of 4 to 6 ⁇ 10 -5 Pa, and finally passed through a special mask on the LiF layer.
  • a 120 nm thick metal Al cathode layer 9 was deposited to prepare a structure of ITO/MoO 3 /TAPC/Ir(ppy) 2 (m-bppy) (7%): BSB/Tb(acac) 3 phen (0.3%): Ir(ppy) 2 (m-bppy) (7%): an organic electroluminescent device of BCBP/TPBi/LiF/Al.
  • the evaporation rate of MoO 3 in the anode modification layer 3 is controlled at 0.02 nm/s
  • the evaporation rate of TAPC in the hole transport-electron blocking layer 4 is controlled at 0.08 nm/s
  • the evaporation rate of TPBi in the hole blocking-electron transport layer 7 is controlled at 0.08 nm/s
  • the evaporation rate of LiF in the cathode modified layer 8 is controlled at 0.02.
  • the evaporation rate of Al in the metal cathode layer 9 was controlled at 1.5 nm/s.
  • the performance of the green organic electroluminescent device prepared in the present example was examined.
  • the experimental results show that the device emits green light at about 515 nm under the driving of a DC power source.
  • the brightness is 20000 cd/m 2
  • the color coordinates of the device are (0.256, 0.649); as the operating voltage changes, the color coordinates of the device are almost unchanged.
  • the device has a starting voltage of 2.9 volts and a maximum brightness of 109152 cd/m 2 .
  • the device has a maximum current efficiency of 120.88 cd/A and a maximum power efficiency of 138.88 lm/W.

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Abstract

Dispositif électroluminescent organique vert composé d'un substrat (1), d'une couche d'anode (2), d'une couche de modification d'anode (3), d'une couche de transport de trous/blocage d'électrons (4), d'une couche émettrice de lumière (5) dominée par les trous, d'une couche émettrice de lumière (6) dominée par les électrons, d'une couche de transport d'électrons/blocage de trous (7), d'une couche de modification de cathode (8), et d'une couche de cathode (9), agencées en séquence; la couche dominée par les électrons (6) est constituée d'un matériau sensibilisé organique, d'un matériau électroluminescent organique vert, et d'un matériau hôte organique de type électronique. Le fait de sélectionner des complexes de terres rares présentant des niveaux d'énergie mis en correspondance, tels que Tb (acac) 3 ou Tb (acac) 3phène, pour le matériau sensibilisé organique, et de doper, à l'aide d'infimes quantités de celui-ci, la couche émettrice de lumière (6) dominée par les électrons, qui a la fonction de centre de liaison profond de porteurs de charge et d'échelle de transport d'énergie, permet d'améliorer l'efficacité d'émission de lumière, la stabilité spectrale, et la durée de vie du dispositif, de réduire la tension de fonctionnement du dispositif, et de retarder l'atténuation de l'efficacité du dispositif.
PCT/CN2014/091784 2014-10-30 2014-11-20 Dispositif électroluminescent organique vert et son procédé de préparation Ceased WO2016065680A1 (fr)

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CN104900815A (zh) * 2015-05-26 2015-09-09 京东方科技集团股份有限公司 双层掺杂磷光发光器件及其制备方法
CN114361355A (zh) * 2022-01-10 2022-04-15 中国科学院长春应用化学研究所 一种顶发射绿色有机电致发光器件及其制备方法
WO2025194343A1 (fr) * 2024-03-19 2025-09-25 京东方科技集团股份有限公司 Matériau pour couche électroluminescente, dispositif d'affichage électroluminescent organique et panneau d'affichage

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